5,6-Didehydro-ω-phenoxy-PGE2 analogs

ABSTRACT

This invention comprises certain analogs of the prostaglandins in which there is a triple bond between C-5 and C-6 or C-4 and C-5. Also provided in this invention, are novel chemical processes useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.

The present application is a divisional application of Ser. No. 619,077,filed Oct. 2, 1975, now issued as U.S. Pat. No. 4,013,695, on Mar. 22,1977.

The present invention relates to prostaglandin analogs for which theessential material constituting a disclosure thereof is incorporated byreference here from U.S. Pat. No. 4,013,695, issued Mar. 22, 1977.

I claim:
 1. A prostaglandin analog of the formula ##STR1## WHEREIN G ISONE, 2, OR 3; WHEREIN Y is trans-CH═CH-;wherein M₁ is ##STR2## whereinR₅ is hydrogen or methyl; WHEREIN T is chloro, fluoro, trifluoromethyl,alkyl of one to 3 carbon atoms, inclusive, or alkoxy of one to 3 carbonatoms, inclusive, and s is zero, one, 2, or 3, the various T's being thesame or different, with the proviso that not more than two T's are otherthan alkyl; Wherein L₁ is ##STR3## or a mixture of ##STR4## wherein R₃and R₄ are hydrogen or methyl being the same or different; and WhereinR₁ is hydrogen, alkyl of one to 12 carbon atoms, inclusive, cycloalkylof 3 to 10 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms,inclusive, phenyl, phenyl substituted with one, two, or three chloro oralkyl of one to 3 carbon atoms, inclusive, or a pharmacologicallyacceptable cation.
 2. A compound according to claim 1, wherein M₁ is##STR5##
 3. A compound according to claim 1, wherein M₁ is ##STR6##
 4. Acompound according to claim 3, wherein g is
 3. 5. A compound accordingto claim 4, wherein m is
 3. 6. A compound according to claim 5, whereinR₃, R₄, and R₅ are all hydrogen. 7.2a,2b-Dihomo-5,6-didehydro-16-phenoxy-17,18,19,20-tetranor-PGE₁, methylester, a compound according to claim
 6. 8. A compound according to claim3, wherein g is one.
 9. A compound according to claim 8, wherein m is 3.10. A compound according to claim 9, wherein R₃ and R₄ are bothhydrogen.
 11. A compound according to claim 10, wherein R₅ is methyl.12. 5,6-Didehydro-15-methyl-16-phenoxy-17,18,19,20-tetranor-PGE₁, methylester, a compound according to claim
 11. 13.5,6-Didehydro-15-methyl-16-phenoxy-17,18,19,20-tetranor-PGE₁, a compoundaccording to claim
 11. 14. A compound according to claim 10, wherein R₅is hydrogen.
 15. 5,6-Didehydro-16-phenoxy-17,18,19,20-tetranor-PGE₁, acompound according to claim
 14. 16.5,6-Didehydro-16-phenoxy-17,18,19,20-tetranor-PGE₁, methyl ester, acompound according to claim
 14. 17. A compound according to claim 9,wherein at least one of R₃ and R₄ is methyl.
 18. A compound according toclaim 17, wherein R₃ and R₄ are both methyl.
 19. A compound according toclaim 18, wherein R₅ is methyl. 20.5,6-Didehydro-15,16-dimethyl-16-phenoxy-18,19,20-trinor-PGE₁, a compoundaccording to claim
 19. 21.5,6-Didehydro-15,16-dimethyl-16-phenoxy-18,19,20-trinor-PGE₁, methylester, a compound according to claim
 19. 22. A compound according toclaim 18, wherein R₅ is hydrogen. 23.5,6-Didehydro-16-methyl-16-phenoxy-18,19,20-trinor-PGE₁, a compoundaccording to claim
 22. 24.5,6-Didehydro-16-methyl-16-phenoxy-18,19,20-trinor-PGE₁, methyl ester, acompound according to claim 22.